Triacetoxyperiodinane → 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone

HRID 1515805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515805
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:20]([OH:27])[CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:20](=[O:27])[CH2:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 672295941-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol

Produkt 1

HCID 672278731-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanoneAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol (2.1 g, 5.4 mmol) in dichloromethane (200 mL) was added Dess-Martin periodinane (5.7 g, 13.5 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 1 h and then quenched with a saturated aqueous sodium bicarbonate solution (100 mL). The mixture was extracted with dichloromethane (50 mL), washed with a saturated aqueous sodium bicarbonate solution (3×100 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash column chromatography (QingDao silica gel, 200-300 mesh, 30% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone (1.6 g, 76%) as a light yellow solid: LC/MS m/e calcd for C20H19FN2O3S [M+H]+ 387.45, observed 387.0.

Aufarbeitung

  1. customquenched with a saturated aqueous sodium bicarbonate solution (100 mL)
  2. extractionThe mixture was extracted with dichloromethane (50 mL)
  3. washwashed with a saturated aqueous sodium bicarbonate solution (3×100 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (QingDao silica gel, 200-300 mesh, 30% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a6ecce28e37c43d49a30d8d2c0ff3665
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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